1985 Men's Quarter-Final
Kevin Curren def John McEnroe 6-2 6-2 6-4
The enfant terrible of tennis was also the ruling patriarch of SW19 in 1985. McEnroe had reached the final of the tournament on every single occasion since 1980 and was the two-time defending champion against number eight seed Kevin Curren.
The previous year, McEnrore had compiled an 82-3 win-loss statistic - a record that stands to this day - and even though 1985 had not been nearly as fruitful, the then 26-year-old was expected to make a serious bid for a third successive Wimbledon title. But he was denied by Curren - a plucky South African who had defeated another defending champion, Jimmy Connors, back in 1983.
The normally fiery American was strangely dull against his unheralded opponent, who took full advantage - raining down aces, and putting away the serves that McEnroe did manage to return with solid volleys. With McEnroe's normally sparkling volleys not finding their lustre, Curren blasted past the number one seed to set up another encounter with Connors in the semis.
This was only the second straight sets loss for McEnroe at Wimbledon and one that heralded the end of his dominance at centre court.
What Curren said: "I'm a much more mature and experienced player since two years ago when I beat Jimmy here. I was nervous back then, but felt more in control today."
What McEnroe said: "He just overpowered me. It was a combination of me being off my game and him just wanting to win. I really felt old out there. I guess it was a pretty difficult thing to cope with, being two sets down, because I didn't seem to cope with it very well. I hope it stays a rare experience for me."
What happened next: Curren caused another huge upset when he thrashed Connors in straight sets in the semis before losing to the even bigger serving Boris Becker in the final. The South African never progressed beyond the fourth round of a Grand Slam again - and eventually retired in 1993. He went on to coach the country's Davis Cup team.
McEnroe lost to Ivan Lendl in the final of the US Open later that year, but then never reached the summit clash of a Grand Slam again as, led by Becker, the age of power began to dawn on tennis. Some observers said that the retirement of McEnroe's great rival, Bjorn Borg, in 1983, took a lot of the fire out of him and made him a far lesser player than he'd been when the Swede had been around to push him to a higher level.
Nonetheless, McEnroe continued playing until 1992 when he made one final splash at Wimbledon where, as an unseeded player, he reached the semi-finals before losing in straight sets to an emerging talent by the name of Andre Agassi.
1999 Women's First Round
Jelena Dokic def Martina Hingis 6-2 6-0
This was an upset second only to Steffi Graf's first-round exit at the hands of Lori McNeil at the same stage five years ago. At the time, Hingis was the dominant force in women's tennis - a crafty genius whose understanding of the court and the angles defied belief. She had won the Australian Open earlier that year, reached the final of the French Open only a fortnight ago, and was the overwhelming favourite to add to her 1997 triummph at Wimbledon.
But in two stunningly one-sided sets - she was swept away by the 16-year-old qualifier Dokic whose powerful strokes from the back of the court were simply too much for the Swiss Miss. This was the first major Hingis appeared in from which her mother, Melanie Molitor, who had mentored and coached her daughter from childhood, was absent due to a parting of ways. For large parts of the match, the number one seed seemed out of focus and unable to concentrate.
Dokic, another prodigy who'd been coached by a parent - father Damir Dokic - took full toll on her illustrious opponent - emerging with the spoils and seemingly on her way to the very apex of the sport.
What Dokic said: "I guess I still can't believe I beat her. "It was a big win for me, coming from qualifying. I thought I played quite well. Even when I won that first set I didn't think it would be easy because one chance and she's going to take it. I knew I had to play well the whole match.
"Just because I beat Hingis doesn't mean I have to come out and win the tournament."
What Hingis said: "If you lose, it doesn't really matter what the score is. Nobody really cares, if you lose.
"This tournament, we decided to have a little bit of distance. [on her mother's absence from the tournament]. We'll probably work a bit more on our private lives and see how it is going to go in the future. We are fine together. We call each other one or two times a day, but don't talk about tennis too much. But it is only three or four days we didn't see each other.
"At the beginning I thought I was really focused and felt in good shape but in a way I was away."
What happened next: Dokic made it all the way to the quarter-finals before falling to Alexandra Stevenson. She never quite lived up to her early promise though - problems with a reportedly over-bearing father along with her tender years when she turned up on the scene combined for a rapid fall. Dokic continues to be active today but has only progressed past the fourth round of a Grand Slam three times since that heady day in London in 1999.
Despite reaching the final of the US Open later than year and three successive Australian Open finals from 2000-2002, Hingis too faded away as her smooth, touch game began to look increasingly out of place in era of power that had now taken root in women's tennis. The Williams sisters, Kim Clijsters, Lindsay Davenport, a more powerful Jennifer Capriati all proved too strong for her and the Swiss retired from the game in 2003 at the age of 22, with injuries playing a huge role in the decision as well.
An ill-judged comeback three years later ended in 2007 when she tested positive for cocaine. The woman who was once touted as the successor to the likes of Steffi Graf ended with five Grand Slams, which is not a bad tally at all. It could, should have been so much more.
2002 Men's Second Round
George Bastl def Pete Sampras 6-3 6-2 4-6 3-6 6-4
It was the second successive year that Sampras fell to a Swiss at Wimbledon in five sets. In 2001, Roger Federer had beaten the great American in what is now considered to be a handing of the baton. Even though that result had been shocking - it wasn't entirely unexpected. Federer had already been anointed by many as the next big thing in tennis. Most had not even heard of Bastl - who had only qualified for the tournament as a lucky loser after Felix Mantilla was forced to retire due to injury.
But on the old Court 2, notoriously known as the Graveyard of Champions, Sampras first fell a set and then two sets down. Here was a seven-time champion - a seven-time champion in the twilight of his career, sure, but still considered far too strong for a player who had never before progressed beyond the second round of a Slam. Some of the spark returned as Sampras took sets third and fourth but when Bastl broke for 5-4 in the final set - there was no coming back.
The swansong of the greatest ever grass-court player Wimbledon has ever seen was a second-round exit at the hands of an unheralded journeyman away from the spotlight of centre-court and Court 1.
What Sampras said: "I'd much rather have played him somewhere where I'm a little bit more comfortable. But it's still a tennis court, still the same dimensions. And, you know, I give him credit. He came out swinging away and played great. But, you know, I had my chances. I just couldn't replay some of the points. Had a few chances maybe there to serve for the match. Just a little -- got a little unfortunate today.
"I'm not going to give into the critics - I'll stop [retire] on my own terms. What I've done here and what I've done to the game is always going to stick no matter what happens in the next few years. But I still believe I have a major in me."
What others said: "That is the worst grasscourt match I have seen Pete Sampras play It is a staggering result, one of the biggest shocks in Wimbledon history." BBC commentator John Lloyd.
What happened next: Bastl retreated into the tennis shadows, never progressing beyond the first round of a Grand Slam.
Sampras never played again at Wimbledon. His words after the loss to Bastl did prove prophetic though - the American won the US Open later that year, his 14th and last major - to seal his legacy as a modern tennis great. Sampras' final year at SW19 also marked the end of serve and volley dominance there. No serve-and-volleyer has won Wimbledon in the decade since.
2011 Men's Quarter-final
Jo-Wilfriend Tsonga def Roger Federer 3-6 6-7 6-4 6-4 6-4
This was not in the mould of your classic upset - Tsonga was in red-hot form at Wimbledon while Roger Federer, while still formidable - was no longer the force who had dominated the manicured lawns for so long.
But then, here are the stats: Prior to this match, Federer had lost only once in five meetings with the Frenchman. Prior to this, Federer had won five Wimbledons, Tsonga had never gone beyond the last eight. Most importantly, prior to this, Federer had never lost a best-of-five match after going two sets up.
And it was all going smoothly when Federer started like a train to take the first set, and then resisted a Tsonga charge in the second to edge the tie-break. He would not see another break point in the entire match as the Frenchman found another gear to his game that even the mighty Swiss could not match.
The final three sets were not as close as they look - every service game was a struggle for Federer, every service game a breeze for Tsonga. When it finished, Federer had lost a five-setter for the first time after being two up.
What Federer said: "When I was 20, I would have been crushed: 'I can't go on; I'll never get another chance to be in a quarterfinal of a Grand Slam.' But today, I know that I should probably have lots more. [The match] wasn't a shocker, second-round loss in straight sets, some stupid match I played.
"It was a great match, I think, from both sides. It's not just his backhand or forehand or serve or physical or mental game -- at the end, it's an overall effort. He was very strong. On the big points, he played his best, he took chances and risks. It's hard to accept, because I thought I was at least as good as he was."
What Tsonga said: "I was feeling really strong because I never -- how you say that? -- panic. I was, all the time, really focused. I'm the kind of player who likes these big moments."
What happened next: The same fate that befell everyone in 2011 hounded Tsonga as well - he lost to eventual champion Novak Djokovic in the next round. The Frenchman continues to be a serious threat at the major tournaments, but there's now a feeling that he'll never achieve the kind of consistency needed to break the top three's stranglehold on the game.
Federer went on to lose another match after being two sets up - the 2011 US Open against Djokovic. The loss was even more heartbreaking, with Federer having two match points on his own serve. The Swiss did conjure up a revival towards the end of the year, winning the year-ending Barclays ATP World Tour Championship and then carrying on the good form into the new year. His two and a half year wait for a major goes on though.